Anticancer properties of naturally occurring (2R, 3R)-(-)-1-methoxyspirobrassinol methyl ether and their synthetic amino analogs inspired us to study the synthesis of new target compounds with a C-C bond in the 2-position of indole rather than a C-N or C-O bond. The goal was efficiently achieved by electrophilic - nucleophilic 3,2-difunctionalisation of 1-methoxybrassinin in the presence of bromine and Grignard reagent leading to the formation of cis-()- and trans-()-C-C analogs of 1-methoxyspirobrassinol methyl ether. The formation of magnesium bromide, during the bromine initiated...